1. Prior Art
U.S. Pat. No. 3,959,368 teaches the compound N,N-dimethyl-N'-phenylthiocarbamyl formamidine and its use as an antiinflammatory.
2. Brief Description of the Invention
The compounds of this invention have the following structural formula: ##STR3## wherein
n is the integer 1,2 or 3, preferably 1 or 2;
R is alkyl having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, more preferably methyl; alkoxy having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, more preferably methoxy; alkylthio having 1 to 4 carbon atoms, preferably methylthio; halogen, preferably chlorine; nitro; acyl having 1 to 4 carbon atoms, preferably acetyl; hydroxyl and ##STR4## wherein R.sup.3 and R.sup.4 have the same meaning as R.sup.1 and R.sup.2 defined below;
R.sup.1 and R.sup.2 are the same or different and are alkyl having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, more preferably methyl or taken together represent the chain --(CH.sub.2).sub.p --(X).sub.m --(CH.sub.2).sub.q and forming a ring structure with the nitrogen to which they are bound wherein p is 1, 2 or 3, q is 2 or 3, X represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.3--, R.sup.3 is hydrogen or alkyl having 1 to 6 carbon atoms, preferably methyl, and m is 0 or 1.
The compounds of this invention can be used for their intended pharmaceutical purposes either as the free base (described above) or in the form of suitable organic or inorganic acid salts. A preferred form is the hydrochloric acid salt.
The compounds of this invention can be prepared according to the following reaction: ##STR5## wherein R, R.sup.1, R.sup.2 and n are as defined.
Generally, the reaction is carried out by dissolving the two reactants in a solvent such as benzene or toluene, heating the solution at reflux for about 15 minutes, slowly distilling off the solvent-methanol mixture, cooling the undistilled solution to room temperature and the recovering of the desired product by filtration. The recovered product can be purified by standard procedures.